Compounds such as nojirimycin (A) and mannojirimycin (B), as shown below, are known to possess antiviral and anticancer properties through glycosidase inhibition. A special feature of these type of compounds is the presence of polyhydroxy cyclic amides in the core structure. Therefore, this proposal is directed towards the synthesis of highly functionalized cyclic amides via intramolecular type III ene reaction. Although the intramolecular ene reaction is well known in the literature since 1930's; its synthetic utility has become recognized only recently. The intramolecular ene reaction also shows very high regio- and chemoselectivity. The study involving the activation of the ene donor has not been studied systematically. So far it has been reported that an electron withdrawing group activates the ene acceptors. Therefore, it is likely than an electron donating group on the ene donor could activate the ene reaction. Therefore, the initial study will involve the synthesis of few model compounds bearing the electron donating group in the appropriate position(s), and study the effect of these activating groups in type III intramolecular ene reaction. The results of these investigations will then be applied to the systems containing an heteroatom, such as nitrogen, and the ene region of these substrates will be studied. Once the viability of the reaction is established for the synthesis of cyclic amides, the methodology will be applied to the synthesis of nojirimycin and their isomers. These polyhydroxy cyclic amides will then be tested for biological activity by using an in-vitro leukemic cell culture techniques. A number of cyclic amides as shown in the Table I will also be synthesized as potential anti-AIDS agents. At the same time two (one junior and one senior level) potential minority undergraduate students will be directly trained through the project in the biomedical research area.